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Ladylike

Roland Bello

Where it began: In 1947 French designer Christian Dior ushered in the lavishly feminine New Look with a nipped-in waist and a full skirt. Grace Kelly and Jackie Kennedy gave it mass appeal in the 1950s, making it the silhouette of choice for well-dressed women.

Why it keeps coming back: It complements curves and looks polished but never over-the-top, says Patricia Mears, the deputy director of the Museum at the Fashion Institute of Technology, in New York City.

How to wear it now: Sophistication lies in the details. Bow-tie kitten heels or vintagey jewelry can effortlessly class up your jeans.

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Ladylike Clothing

Roland Bello

How to wear it now: Try separates rather than the traditional fit-and-flare dress. “A blouse-and-skirt combo looks even more modern,” says Brooke Jaffe, the fashion director of women’s accessories for Bloomingdale’s. For evening wear that is equally glamorous and comfortable, pair a wrap shirt with an embellished, twirly skirt.

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Animal Prints

Roland Bello

Where it began: When Europeans began colonizing Asia and Africa in the 18th century, they brought home the skins of the leopards, tigers, and zebras that they found there. Those exotic patterns were soon reproduced on fabrics (for the über-rich, of course), leaving their mark on clothing and decor. Two centuries later, sex symbols like Lauren Bacall and Marilyn Monroe harnessed the prints’ come-hither magnetism.

Why it keeps coming back: Animal prints are like neutrals—they’re made up of brown, beige, and black, after all. “They’re seasonless, and you can wear them with almost anything,” says Jaffe. Plus, they add a little edge to your wardrobe.

How to wear it now: Hit the spot in small doses if you fear the print will swallow you whole; animal print accessories, like those shown here, can be just as eye-catching.

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Animal-Print Clothing

Roland Bello

How to wear it now: “This season, you’ll see animal prints that are more graphic or magnified,” says Jaffe. Try a patterned piece with a solid jewel tone to keep it out of retro territory. An ocelot pattern like this coat’s is plenty wild, so stick with a silhouette that is simple, sleek, and tasteful.

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Menswear

Roland Bello

Where it began: Thank designer Coco Chanel, who popularized pants for women in the 1920s. She also gets points for making sportswear separates, like jersey jackets and cardigans, that were designed to be stylish and comfortable on the go. Not far behind her: actress Katharine Hepburn, a trailblazer for the tomboy look in the ’30s; and ’70s musician Patti Smith, who added a little rock and roll to the mix.

Why it keeps coming back: “You might expect menswear to be desexualizing, but it’s often the opposite,” says Sharon Graubard, the senior vice-president of creative services at the trend-forecasting agency Stylesight, in New York City. Menswear is flattering on almost any shape or size, and it works in or out of the office.How to wear it now: Dapper touches, like a fedora or a chunky watch, easily swing the other way and mingle with frilly dresses.

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Menswear-Inspired Clothing

Roland Bello

How to wear it now: Choose fitted, not oversize, cuts. And contrast seriously sharp tailoring with fun, feminine accents. Daring jewelry and colorful high heels will do it. For a night out, a tuxedo jacket and tie-print pants are unexpectedly posh (and relaxed).

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Minimalism

Roland Bello

Where it began: French designers André Courrèges and Pierre Cardin made mod shift dresses in the 1960s (model Twiggy was a fan), and Halston kept the streamlined silhouette going in the ’70s with monochromatic jersey dresses and stretchy jumpsuits. But in the ’90s it was Miuccia Prada who had the most staying power. Her simple shapes and sparse ornamentation were a welcome palate cleanser after the huge shoulder pads (and hair) of the ’80s, and they’re still popular today.

Why it keeps coming back: “Clean lines and functionality have always been hallmarks of American style,” says Mears. Audrey Hepburn’s Capris are a classic example of this intersection of élan and ease.

How to wear it now: Pick one powerful piece (a geometric scarf, a sculptural cuff) and let it pop against something basic.

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Minimalist Clothing

Roland Bello

How to wear it now: Pieces are still pared down but have bold details (like the asymmetrical seam seen here). Look for a striking hem or neckline and sharp cutouts. And when black and white collide, you get major impact—meaning no need for a lot of accessories.

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Florals

Roland Bello

Where it began: With Mother Nature, really. Flowers-as-adornment is as old as the hills. But in terms of being painted or printed on clothing, blossoms were seen on Japanese kimonos around the year 794 and on rich Genoese velvets in the 1400s.

Why it keeps coming back: In a word, pretty. “We always think of a flower as the symbol of a woman,” says Mears. And there are countless interpretations to appeal to any taste—from soft, watercolor petals to full-on flower power, as worn by ’60s model and “it girl” Jean Shrimpton.

How to wear it now: For a subtle approach, spruce up any old cardigan with a lively brooch or scarf.

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Floral Clothing

Roland Bello

How to wear it now: What’s fresh? Less lavender, more aubergine. “Florals are cropping up in deeper autumnal tones,” notes Graubard, which makes them appropriate no matter how ungirlie you may be. Mix patterns? By all means. Just make sure there’s one color, like black or navy, that links both prints together.

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Military

Roland Bello

Where it began: During World War II, civilians, even ladies, took to wearing government-issue trench coats as everyday outerwear. And in the Vietnam era, young people in the antiwar movement appropriated fatigues—camouflage, army jackets, cargo pants—as symbols of protest. They became trendsetters in the process. Before long, the fashion elite, like model Lauren Hutton, started sporting the look.

Why it keeps coming back: It’s functional, for one thing. And, like menswear, it has a tough, androgynous appeal. Who knew something called “olive drab” could be so versatile and rich?

How to wear it now: Adding an accessory or two is all you need to get a casual outfit into high gear.

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Military Clothing

Roland Bello

How to wear it now: Remember—it’s an outfit, not a uniform. Look for details like cargo pockets, epaulets, and insignias (think high-style Boy Scout badges). But avoid too many at once. You want to look contemporary, not literal. A dashing cape, like this one, is best layered over slim-fitting styles.